History, Nature & Small Town Charm
New England is known for its fresh seafood, fall foliage and quaint historic charm. What better way to explore it than a road trip to Cape Cod, Massachusetts where picturesque towns brush up against cutting-edge oceanographic research?
The Cape Cod National Seashore is only a 2.5-hour drive from Boston, so the best way to visit is a two- or three-day road trip from the Boston area. Of course, you can just as quickly start the trip from Providence, Rhode Island, or even New York City and adjust your route accordingly!
For the best weather, visit in the spring or summer, but even sunny days can be windy or rainy along the Atlantic coast. If you want to see the leaves change color in the fall, plan to visit between September and October. Many of the activities on this itinerary are seasonal, so don’t be surprised to find some things closed if you go in the off-season (Labor Day through Memorial Day).
Start: Boston, Massachusetts
Cape Cod has several regional airports, but you’ll have the most options if you fly into Logan International Airport in Boston and rent a car there. Boston is a popular destination in its own right, so if you have the time, plan to spend an extra day in the city exploring the sights.
Families will want to check out the New England Aquarium or the Museum of Science, while couples can have a romantic Italian dinner at Prezza in the North End. Wherever you go, you’ll be reminded of Boston’s historic past, immortalized in the city’s famous Freedom Trail and the Bunker Hill Monument.
If you need accommodations in town, stay at the Verb Hotel near Fenway Park, featuring retro rock-and-roll decor and in-room record players.
Day 1 – Boston to Plymouth
It’s time to drive! Wake up early for the trip from Boston to Plymouth. Although it’s only an hour away, you’ll want to get on the road early because there’s a lot to see and do—including journeying back in time!
Rewind to 1620, the year when Plymouth was first settled by Europeans. See the site where the Pilgrims allegedly landed, Plymouth Rock or take a tour of the Mayflower II, a re-creation of the ship that carried them to America.
Kids will love Plimoth Patuxet, a family-friendly living history museum where you can explore a model English settlement and interact with role players in authentic period costumes. Adults may prefer the Pilgrim Hall Museum—the “oldest public museum” in the country —or the Plimoth Grist Mill, which still mills flour the old-fashioned way!
No trip to Plymouth would be complete without enjoying some local New England seafood. The Lobster Hut serves regional items such as lobster rolls and stuffed quahogs in a casual, open-air setting right on the wharf.
Couples can end the day with a “date night” package at Hotel 1620, or drive directly to the next stop to spend more time on the Cape. The Sea Crest Beach Hotel is the only waterfront property on the Cape, with guest rooms, suites and cottages to choose from.
Day 2 – Plymouth to Provincetown
The drive from Plymouth to Provincetown only takes an hour and a half, but part of the fun is stopping in small towns along the way. You’ll also get your first glimpse of Cape Cod National Seashore, which encompasses more than 43,000 acres including the area surrounding Provincetown.
When it comes to small towns, Sandwich is a highlight, with attractions like the Heritage Museums & Gardens and the Sandwich Glass Museum, where you can see glass blowers at work and pick up some souvenirs to take home. Another option is to stop at the Woods Hole Oceanographic Institute, where you can learn about the REMUS SharkCam and other marine research projects.
Aim to get to Provincetown around lunchtime so you can visit the Pilgrim Monument and Provincetown Museum before catching a whale watching trip. At the museum, learn about everything from the relationship between pilgrims and the Wampanoag Nation, to the history of the town’s first fire engine! Afterwards, book a sunset whale watching tour with the Dolphin Fleet of Provincetown—even a glimpse of these marine mammals is truly magical. Departure times vary, but during the summer months, the last departure is usually at 4 p.m.
Spend the evening wandering the streets of Provincetown, a welcoming tourist town that’s known for its LGBTQ+ community and vibrant arts scene. The Provincetown Theater puts on performances of well-known plays like The Glass Menagerie and Sweeney Todd, while the Crown & Anchor hosts singalongs and variety shows.
Stay in town at the upscale Eben House, or head to the Truro Cottages for a relaxing and secluded getaway right on the beach.
Day 3 – Cape Cod National Seashore
Start the day off with a coffee and pastry at the Provincetown Portuguese Bakery, which sells deep-fried malassadas and other treats from the other side of the Atlantic. Today is your day to enjoy the great outdoors, so make sure to fill up!
If you enjoy beautiful walks and hiking in general, visit the Wood End Lighthouse. Extending across the bay and leading to a secluded beach, the Provincetown Causeway offers a scenic route to get to the lighthouse. For a more laid-back morning by the sea, swim, sunbathe and stroll along Race Point Beach. Located at the tip of the Cape, this is just one of six beaches within Cape Cod National Seashore.
Next, get ready to explore on two wheels. Go for a leisurely bike ride on the Cape Cod Rail Trail, a 25-mile paved route that will take you through some of the Cape’s most scenic areas, such as Nickerson State Park. The Idle Times Bike Shop has multiple locations along the trail, so you can start at any section of the trail that you like. Rentals start at $30 for 24 hours.
If you’re still up for an adventure after your bike ride, learn how cranberries are grown on a 1.5-hour Cranberry Bog Tour. And if you come during the fall, you may even see the bogs flooded with water as workers harvest the floating cranberries. Visit the Farm Stand afterward for delicious cranberry-related souvenirs to take home!
Finally, sample some local wines at First Crush Winery—paired with a local cheese and cracker plate, of course—before heading back to Boston to conclude your New England road trip.